The instant invention relates to alkyl-substituted-oxo-spirodecenene derivatives defined according to the structure: ##STR2## wherein X represents carbinol, carbinol C.sub.1 -C.sub.3 alkanoate or ketone; wherein one of R.sub.1, R.sub.2, R.sub.4 and R.sub.5 represents methyl and the other of R.sub.1, R.sub.2, R.sub.4 and R.sub.5 each represent hydrogen; and R.sub.3 represents n-butyl or isopropyl and uses of same in augmenting or enhancing the aroma of perfume compositions, perfumed articles and colognes.
Inexpensive chemical compounds which can provide cardamon, figgy, date-like, vetiver, floral, rose, woody, musky, incense-like, olibanum, spicy, camphoraceous, natural balsamic and lemony aromas with spicy, minty, fruity, rose, sweaty, animalic, sweet, musky, floral, jasmine and fatty topnotes are highly desirable in the art of perfumery. Many of the natural materials which provide such fragrances and contribute such desired nuances to perfume compositions as well as perfumed articles are high in cost, unobtainable at times, vary in quality from one batch to another and/or are generally subject to the usual variations of natural products.
There is, accordingly, a continuing effort to find synthetic materials which will replace, enhance or augment the fragrance notes provided by natural essential oils or compositions thereof. Unfortunately, many of the synthetic materials either have the desired nuances only to a relatively small degree or they contribute undesirable or unwanted odor to the compositions.
Spiro ketones are known in the prior art and their utilities in many instances are known in perfumery.
Thus, Japanese Published Application 76/65738 (abstracted at Chemical Abstracts 85:123440f) (corresponding to U.S. Pat. No. 4,052,457 issued on Oct. 4, 1977) discloses the compound having the structure: ##STR3## as being useful in perfumery and further discloses the process according to the reaction: ##STR4##
Nerdel and Dahl, Ann. Chim., 710, 90 (1967) discloses the compound having the structure: ##STR5## and the generic process, to wit: ##STR6## (wherein R represents hydrogen or methyl).
Tanaka, et al, Chem.Comm. 1967, page 188 (title of paper: "The Total Synthesis of Chamigrene" discloses the compound having the structure: ##STR7##
U.S. Pat. No. 4,261,866 issued on Apr. 14, 1981 (Class 252, Subclass 522R) discloses the genus of compounds having the structure: ##STR8## wherein R.sub.1 -R.sub.6 each represents hydrogen or lower alkyl. U.S. Pat. No. 4,261,866 further discloses the broad genus, to wit: ##STR9## wherein each of the dashed lines represent carbon-carbon single bonds and carbon-carbon double bonds. The compounds disclosed in U.S. Pat. No. 4,261,866 are indicated to be useful in perfumery.
However, the alkyl-substituted-oxo-spirodecenene derivatives of our invention have unexpected, unobvious and advantageous perfumery properties when compared with the perfumery properties of the above-cited prior art.
In addition, copending application for United States Letters Patent, Ser. No. 805,739 filed on Dec. 6, 1985 assigned to the assignee of the instant application, International Flavors & Fragrances Inc., relates to alkyl-substituted spiro undecenone derivatives defined according to the structure: ##STR10## wherein R.sub.1 represents isopropyl or hydrogen and R.sub.2, R.sub.3 and R.sub.4 are each the same and each represents methyl or hydrogen; with the provisos:
(i) that when R.sub.1 is isopropyl, R.sub.2, R.sub.3 and R.sub.4 are hydrogen; and PA1 (ii) when R.sub.2, R.sub.3 and R.sub.4 are methyl, R.sub.1 is hydrogen,
and uses of same in augmenting or enhancing the aroma of perfume compositions, perfumed articles and colognes.
The structures of the compounds of application for U.S. Letters Patent, Ser. No. 805,739 filed on Dec. 6, 1985 are different in kind rather than degree from the structures of the alkyl-substituted-oxo-spirodecenene derivatives of our invention.